I suggest you manually define masks (yellow, red and transparent squares) for every dwelling ("visitableFrom" may stay as base for every dwelling). Look: castle's dwellings have various masks.
For example - mask for Halbardiers' dwelling is [ "VVV", "VBV", "VBA" ] , for Angels' dwelling is [ "VVVV", "VBAV" ], for monks' dwelling is [ "VVV", "VVV", "VBA" ] and so on.

VCMI copies all dwelling masks from Guardhouse (first on the list). The problem is that Random Dwellings objects may become inaccessible if different mask is picked:
http://bugs.vcmi.eu/view.php?id=900

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DJ Warmonger blog

I have bmp file with my adventure map objects. I open Def maker, load this bmp in it and click reposition tab.

So you can see 20 square parts in four rows. Each row has 5 squares.
And you have three mask parameters.
V - visible, transparent square
B - blocked square (red in map editor)
A - visitable by hero square (yellow in map editor)

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